Methanol → HCID 44187342, compound

HRID 1802817Notes

Reaction equation

HRID 1802817 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[NH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.O.CO.O.[OH-].[Li+]>O1CCCC1>[Cl:19][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([NH:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:14]=1)[NH:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][CH:6]=1)=[CH:18]2

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 44187341HCID 44187341, compound

Product 1

HCID 44187342HCID 44187342, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound obtained in Example 64 (300 mg, 0.81 mmol) was dissolved in 15 ml of tetrahydrofuran, 5 ml of water and 5 ml of methanol. 100 mg (2.44 mmol) of Lithium hydroxide monohydrate was added. The mixture was stirred at room temperature for 21 hours. At the end of reaction, tetrahydrofurane and methanol were removed by distillation under reduced pressure. To the distillate 1N HCl solution was added the mixture was extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered. The filtrate was distilled under reduced pressure, and separated by column chromatography to obtain the title compound 20 mg (Yield 7%).

Workup

  1. customwere removed by distillation under reduced pressure
  2. additionTo the distillate 1N HCl solution was added the mixture
  3. extractionwas extracted with ethylacetate
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customseparated by column chromatography

Sources & evidence

ORD record
ord-a1d610513f5742909024c0b70f8446a2
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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